Why Women Cheat: A Married Man Goes Undercover On Ashley Madison

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A married relationship expert joins Ashley Madison and learns a valuable love lesson.

"Honey, I have to join Ashley Madison."

So began the pitch I gave my wife to let me join the marrieds-looking-for-affairs website, AshleyMadison.com. It would be part of my research into women who cheat, why infidelity is increasing, and what can be done to possibly affair-proof a marriage. I proposed to "cheat" on her for a few weeks, to talk to and attempt to seduce as many women as possible, and get a real-world understanding of why women want to stay married but also need some illicit action on the side.

Of course, on my end, there'd be nothing more than conversation. She looked at me straight-faced, unflinching. I searched her eyes for any telltale sign of the Charles-I'm-going-to-punch-you-in-the-face-right-after-I-castrate-you look; nothing. After a long pause, I got her only thought: "No, I get it," she said emphatically. "It's a great story. But it's kinda like asking the newly-vegetarian fox to guard the henhouse, isn't it?" 

I thought about it, and unfortunately her statement wasn't too far from the truth. If you back me up a few years—sans wife, kids, dogs, published book on relationships, 400,000+ fans following my relationship advice on Facebook—I was a chronic womanizer; a past she knows about, but never experienced personally. To make matters worse, I wasn't some weak pick-up artist using idiotic dating boot camp approaches that reeked of negativity and douchebaggery on vulnerable women in order to break them down and manipulate them into sex. No… I was far more despicable than that. 

Was I looking to get women into bed? Of course, but it was more than that. I worked hard to become the embodiment of seduction. To quickly read the spoken and unspoken clues of what a woman was looking for in a man, and then give her the perception I was that guy. In effect, to become so alluring that she would willingly give herself over, thinking that having sex was her idea. After all, it's much easier to convince people of things they think they have thought of themselves. It was quite a rush, and as the wake of emotional destruction would later exemplify, seducing women became my drug of choice.

"No, babe ... that's not even close," I told her, not fully considering the implications of the coming situations. "That was 15… no, almost 20 years ago. And you know that I love you. There's nothing to fear."

After another pregnant pause, she consented with a few words of sage advice:

"Don't. Fuck. Up."


The Statistics

According to The Journal of Couple and Relationship Therapy, nearly 50 percent of married women and 60 percent of married men will have an extramarital affair at some point in their marriage. When you consider that these statistics are nearly double what they were a short 10 years ago, clearly this is beyond an issue; it is now commonplace. But it's far from a surprise; it was predicted. Futurist Alvin Toffler wrote the best seller Future Shock in 1970, and with matter-of-fact conviction he wrote of "trial" or "temporary marriages"—young people's first marriages, lasting three months to three years—and of "serial marriages" that would take place after the dissolution of the "trial marriage" at specific turning points in people's lives. 

So, does this mean marriage has "jumped the shark" and become obsolete? Hardly. Marriage is not the issue. Commitment and loyalty or the lack thereof are at the crux of this. After all, marriage is a legal and/or spiritual binding of two people… but if commitment isn't there and loyalty becomes a matter of subjectivity or convenience, the marriage is already nonexistent. Cheating then becomes a symptom of a secretly failed marriage.

But is it really so black and white, with no grey and no room for mistakes, missteps, or moments of weakness? Do people who cheat want to leave their current marriage? Are they secretly trying to get caught so they'll have an excuse to get out? I needed answers to these questions (and many others), so I headed where any high-tech junkie looking to cheat on his wife would go: online.

The Business of Infidelity

The advent of the Internet has made having an illicit affair easier than ever before. Meeting Mr. or Ms. Right, The Sequel, is a mere mouse-click for anyone with a credit card. If you're looking to Hit-It-And-Quit-It, there's AdultFriendFinder.com, Craigslist's Casual Encounters or Fling.com (among many others). But sex-only semi-anonymous hookups wasn't where my investigation was headed, as women looking to merely have sex can meet a man anywhere—nightclubs, coffee shops, Facebook, wherever.

My hypothesis was simple: women who were looking for an extramarital affair with another married man were looking to connect in some way. If both parties were married, they not only started on even ground, but they had something in common—they were missing something from their current relationship. I needed to uncover the motivations behind starting and maintaining an affair.

And affairs are big business. Numerous websites are dedicated to connecting those looking to engage in flagranté delecto sans spouse. AffairsClub.com, MarriedCafe.com, LonelyWivesAffairs.com are but the tip of the iceberg, and all have women and men signing up in droves. The undisputed leader for cheating is AshleyMadison.com, the "Life is short. Have an affair." website. AshleyMadison has experienced meteoric growth since its founding in 2002, with no slowing in sight. And while founder and CEO Noel Biderman doesn't condone having an affair, he seems perfectly comfortable with others doing their infidelity thing. Works for some ... and now, it was my turn to get my (feigned) cheat on.


"Hello, Ashley Madison! Long time, no cheat!"

I filled out my nickname and relevant info, plopped down my credit card number (discretely billed as "AMDB" to my credit card statement), and then all I needed to do was ... wait a second. I was faced with the eternal online seduction dilemma: now what? What will make the opposite sex want me online? What do women want to see on my profile?

Recent reports state that Ashley Madison has a community that is comprised of 70 percent men and 30 percent women. Clearly women have the upper hand with choice, so I needed to stand out against all the other guys. I posted a real picture of me (I was looking to connect in-person, after all), but I listed a fake name (if they Googled my real name, I was sure to be caught). To formulate the right approach, I decided to do something I couldn't do in the real world: get into the minds of my competition, albeit a little sneakily.

I signed up for a second Ashley Madison account as a woman, "Shelly," and began checking out the guys' profiles. Most of the men's profiles highlighted attempts at humor, asking straight-out for sex, to ... uh ... romance ("I like walks on the beach.") Really?! Walks on the beach?! Come on, now ... no, you don't! I mean, we all like walking on the beach, but that's not why you're on the site. And besides, the 1970s called, and they want their pick-up line back. In contrast, so many of the women's profiles were dripped with laments ranging from "lack of attention" to "seeking excitement" to "need someone who pays attention." Additionally, it was fascinating to see "Shelly's" inbox fill up in a matter of minutes. I hadn't even added a picture or completed the profile for that persona.

With a firm understanding of where my competition played—and the miserable approaches of some—I got to work writing something unique, confident, and (hopefully) mysterious and seductive. I set up three profiles to see which would resonate the fastest and which would hit with the most success. "Scottie" was unsure, shy, and a bit weak ("I'm not sure why I'm here."), "Greg" was the quintessential Alpha Male ("You know you want me…"), and the aforementioned "Cameron" was closer to the middle ("Too many men get comfortable—even complacent—and forget that foreplay starts outside the bedroom... that kisses can start soft with cheek strokes, but end with the back of her hair being pulled in wild passion.").  Keep reading...

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Charles J. Orlando

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